Cesium carbonate → 1-(2-Chloro-4-pyrimidinyl)-3-ethyl-2-oxo-3-pyrrolidinecarbonitrile

HRID 714781Notes

Reaction equation

[CH2:1]([C:3]1([C:9]#[N:10])[CH2:7][CH2:6][NH:5][C:4]1=[O:8])[CH3:2].[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Cl:11][C:12]1[N:17]=[C:16]([N:5]2[CH2:6][CH2:7][C:3]([CH2:1][CH3:2])([C:9]#[N:10])[C:4]2=[O:8])[CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 3-ethyl-2-oxopyrrolidine-3-carbonitrile (40 mg) obtained in Step H of Example 1, 2,4-dichloropyrimidine (86 mg), cesium carbonate (190 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mg) in tetrahydrofuran (1 mL) was added tris(dibenzylideneacetone)dipalladium(0) (5 mg), and the mixture was stirred overnight at 100° C. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (46 mg).

Workup

customThe insoluble substance was removed by filtration through Celite
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-1edf98398d5d46be90992d32d3a9087f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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